Baileys Harbor Schoolhouse Inn

Formerly Orphan Annie’s. Our historic 1917 schoolhouse boasts large suites filled with unique details each having a private entrance, bath and deck along with A/C and satellite TV. All rooms include kitchenettes or full-kitchens (coffee pot, toaster, microwave, refrigerator, dishes and utensils) along with a gas grill on- site. Located in a residential neighborhood, the inn is a quiet retreat but still within walking distance of community attractions. Enjoy this authentic local experience hosted by a fifth-generation Baileys Harbor family!

Categories: Hotel/Motel/Inn, Cottage/House


2019 Rates: $985-$1975 weekly; $155-$295 daily.

Winter Hours

Closed in winter


  • Air Conditioning
  • Bed Linens furnished
  • Coffee Service (in unit)
  • Deck
  • Downtown
  • Grill
  • Hair Dryer
  • Hiking Trails
  • Kitchen Facilities
  • Microwave
  • Packages
  • Private Baths
  • Refrigerator
  • Satellite Television
  • Suites
  • Sundeck
  • Wet Bar

Reviews & Ratings

More Information

Located in the heart of Baileys Harbor, one block off Highway 57, the inn is within walking distance of two dozen restaurants, businesses and public parks.  But, our quiet neighborhood is centrally located for easy access to all of Door County! 

Unique suites celebrate the historic architecture of the building.  Many have twelve-foot ceilings and high schoolhouse windows. Our suites are also quite large -- three are 450 square feet, three are 800 square feet, and one is 1100 square feet.  Each is well-appointed to encourage longer stays with some guests staying as long as a full month.

The inn is an excellent choice for small groups – most suites sleep at least four with some hosting up to seven.  Multiple couples traveling together can combine suites to maintain privacy, but facilitate shared spaces. 

Because the inn is family-owned and operated, the guest experience is handled directly by the owners of the inn!  Your clean and quiet stay is made possible because the inn is pet-free, smoke-free and all guests are registered!
Operated by BH Schoolhouse LLC - PO Box 168, Baileys Harbor, WI 54202

Kristen Peil and Caleb Whitney, proprietors.

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